2-Meth­oxy-4-[1-(4-meth­oxy­phen­yl)-4,5-diphenyl-1H-imidazol-2-yl]phenol

Nagaraj, S.; Loganathan, N.

doi:10.1107/S2414314626003160

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 3| March 2026| x260316

https://doi.org/10.1107/S2414314626003160

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2-Methoxy-4-[1-(4-methoxyphenyl)-4,5-diphenyl-1H-imidazol-2-yl]phenol

Seeralan Nagaraj ^a and Nagarajan Loganathan ^a,^b ^*

^aSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India, and ^bUGC Faculty Recharge Programme, New Delhi, India
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 20 March 2026; accepted 24 March 2026; online 27 March 2026)

The title compound, C₂₉H₂₄N₂O₃, was synthesized via a four-component Debus–Radziszewski reaction, involving benzil, amine, aldehyde and ammonium acetate. The OH group of the vanillin substituent forms both an intramolecular and an intermolecular hydrogen bond, the latter generating [010] chains. The extended structure is consolidated by weak C—H⋯O and C—H⋯π interactions, generating a criss-cross motif.

Keywords: crystal structure; Debus–Radziszewski reaction; criss-cross packing pattern.

CCDC reference: 2263383

Structure description

Imidazole is one of the widely studied classes of heterocyclic compounds owing to their immense importance in various physiological process and several enzymatic reactions (Ebel et al., 2026 ). As part of our studies in this area, we reacted diphenylethanedione (commonly known as benzil), 4-hydroxy-3-methoxybenzaldehyde (also known as vanillin), 4-methoxyaniline and ammonium acetate (1:1:4:4 ratio) in glacial acetic acid under overnight reflux conditions. The isolated white solid was found to be the title compound,C₂₉H₂₄N₂O₃ (1) formed in 60–65% yield. This multicomponent reaction is also known as Debus–Radziszewski reaction and was originally reported between 1858–1882 (Debus, 1858 ; Radziszewski, 1882 ); while it was originally attempted to synthesize the 1,2,4-trisubstituted imidazole in the presence of ammonia, the use of ammonium acetate afforded the 1,2,4,5-tetra-substituted imidazole (Wang et al., 2017 ).

Compound (I) crystallizes in the orthorhombic space group P2₁2₁2₁ with one molecule in the asymmetric unit. Earlier, we reported the analogous compound 1-(4-bromophenyl)-4,5-diphenyl-2-(1H-pyrrol-2-yl)-1H-imidazole (II) (Seeralan & Nagarajan, 2026 ) and the geometrical data for (I) are in good agreement with those for (II) as well as similar 1,2,4,5-tetrasubstituted imidazole derivatives reported elsewhere (Xiao et al., 2012 ; Zhao et al., 2012 ). The molecular structure of (I) (Fig. 1) shows that the central C7–C9/N1/N2 imidazole ring is substituted with C16–C21 4-methoxyphenyl (anisole), C10–C15 4-hydroxy-3-methoxyphenyl (vanillin) and two phenyl groups (C1–C6 and C22–C27) at positions 1, 2, 4 and 5, respectively. The dihedral angles between the imidazole ring and the rings of the substituents are 62.66 (7), 40.37 (7), 42.22 (6) and 50.75 (8)°, respectively. The phenyl rings are not coplanar [56.55 (6)°] while the vanillin and 5-phenyl rings are almost perpendicular to each other [88.68 (7)°]; the anisole and 4-phenyl rings subtend a dihedral angle of 79.11 (8)°. An intramolecular O2—H2A⋯O1 hydrogen bond (Table 1) closes an S(5) ring.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C9/N1/N2 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.82	2.28	2.718 (3)	114
O2—H2A⋯N2ⁱ	0.82	2.11	2.809 (3)	143
C4—H4⋯O2ⁱⁱ	0.93	2.55	3.379 (4)	148
C29—H29C⋯Cg1ⁱⁱⁱ	0.96	2.98	3.526 (5)	118
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) ; (iii) $[-x-1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
The molecular structure of (I) showing 50% displacement ellipsoids.

In the extended structure of (I), the same OH group also forms an intermolecular link to N2, generating [010] chains and weak C—H⋯O and C—H⋯π links (Table 1) consolidate the structure, which resembles a criss-cross grid when viewed down [001] (Fig. 2).

Figure 2
Perspective view along c-axis direction showing the supramolecular architecture.

Synthesis and crystallization

The reaction of benzil (1.5324 g 7.28 mmol), vanillin (1.1076 g, 7.28 mmol), 4-methoxyaniline (3.5470 g, 28.8 mmol) and ammonium acetate (3.7554 g, 28.8 mmol) in 35 ml of glacial acetic acid under overnight reflux condition, followed by quenching the reaction mixture in a crushed ice bath afforded a silvery precipitate that was filtered and purified by column chromatography using silica gel (hexane and ethylacetate (9:1) as eluent). Yield 65–70%, m.p. 225°C. FT–IR (cm⁻¹) 3248(br), 2999(w), 2934(w), 2835(w), 1603(s), 1547(s), 1454(s), 1384(s), 1326(m), 1272(w), 1244(m), 1195(s), 1078(s), 1023(s), 974(s), 863(s), 787(m), 741(s) 620(m), 568(m). Yellow blocks of (I) were recrystallized from solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound hydrogen atoms were included in idealized positions (C—H = 0.93–0.96 Å) and the O—H proton was located in a difference-Fourier map. The C28 methyl group of the vanilin substituent is disordered over two sets of sites.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₉H₂₄N₂O₃
M_r	448.50
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	300
a, b, c (Å)	9.9346 (4), 9.9936 (6), 23.9388 (14)
V (Å³)	2376.7 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.31 × 0.24 × 0.17

Data collection
Diffractometer	Bruker D8 QUEST diffractometer with PHOTON II detector
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.613, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	30742, 5416, 4699
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.102, 1.05
No. of reflections	5416
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16
Absolute structure	Flack x determined using 1682 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.3 (3)
Computer programs: APEX4 and SAINT (Bruker, 2012 ), SHELXT (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ), ORTEP-3 for Windows(Farrugia, 2012 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2263383

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626003160/hb4560sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626003160/hb4560Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626003160/hb4560Isup3.cml

checkCIF report

Computing details top

(I) top

Crystal data top

C₂₉H₂₄N₂O₃	D_x = 1.253 Mg m⁻³
M_r = 448.50	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9869 reflections
a = 9.9346 (4) Å	θ = 2.2–27.0°
b = 9.9936 (6) Å	µ = 0.08 mm⁻¹
c = 23.9388 (14) Å	T = 300 K
V = 2376.7 (2) Å³	Block, yellow
Z = 4	0.31 × 0.24 × 0.17 mm
F(000) = 944

Data collection top

Bruker D8 QUEST diffractometer with PHOTON II detector	R_int = 0.036
Radiation source: i-mu-s microfocus source	θ_max = 27.5°, θ_min = 2.2°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −12→12
T_min = 0.613, T_max = 0.746	l = −31→23
30742 measured reflections	5 standard reflections every 18 reflections
5416 independent reflections	intensity decay: none
4699 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0408P)² + 0.4588P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.102	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.18 e Å⁻³
5416 reflections	Δρ_min = −0.16 e Å⁻³
317 parameters	Absolute structure: Flack x determined using 1682 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.3 (3)
Primary atom site location: structure-invariant direct methods

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.5463 (2)	0.1525 (3)	0.22051 (7)	0.0765 (7)
O2	0.31259 (19)	0.0770 (2)	0.27049 (7)	0.0622 (5)
H2A	0.342641	0.057331	0.239659	0.093*
N1	0.68501 (19)	0.46222 (18)	0.43096 (7)	0.0394 (4)
N2	0.70617 (19)	0.54653 (18)	0.34589 (8)	0.0407 (4)
C1	0.8642 (3)	0.7350 (2)	0.36209 (10)	0.0461 (6)
C2	0.9950 (3)	0.7539 (3)	0.38112 (12)	0.0618 (7)
H2	1.029536	0.697210	0.408376	0.074*
C3	1.0743 (4)	0.8552 (4)	0.36031 (16)	0.0822 (10)
H3	1.161184	0.866786	0.373913	0.099*
C4	1.0269 (5)	0.9378 (4)	0.32036 (16)	0.0920 (12)
H4	1.081394	1.005382	0.306137	0.110*
C5	0.8989 (5)	0.9220 (4)	0.30086 (16)	0.0981 (13)
H5	0.866330	0.979097	0.273332	0.118*
C6	0.8161 (4)	0.8204 (3)	0.32197 (12)	0.0731 (9)
H6	0.728567	0.810924	0.308770	0.088*
C7	0.7808 (2)	0.6230 (2)	0.38271 (9)	0.0392 (5)
C8	0.6503 (2)	0.4513 (2)	0.37591 (9)	0.0387 (5)
C9	0.7683 (2)	0.5741 (2)	0.43559 (9)	0.0386 (5)
C10	0.5643 (2)	0.3459 (2)	0.35161 (9)	0.0386 (5)
C11	0.5991 (2)	0.2961 (2)	0.29921 (9)	0.0440 (5)
H11	0.678318	0.324721	0.282301	0.053*
C12	0.5180 (2)	0.2053 (3)	0.27206 (9)	0.0460 (5)
C13	0.3980 (2)	0.1630 (2)	0.29622 (9)	0.0437 (5)
C14	0.3660 (2)	0.2086 (3)	0.34894 (10)	0.0464 (6)
H14	0.288074	0.177873	0.366230	0.056*
C15	0.4473 (2)	0.2990 (2)	0.37655 (9)	0.0443 (5)
H15	0.423533	0.328613	0.412033	0.053*
C16	0.6526 (2)	0.3704 (2)	0.47513 (9)	0.0393 (5)
C17	0.6976 (3)	0.2397 (2)	0.47171 (10)	0.0504 (6)
H17	0.746010	0.211452	0.440637	0.061*
C18	0.6704 (3)	0.1517 (3)	0.51445 (12)	0.0618 (7)
H18	0.700261	0.063711	0.512093	0.074*
C19	0.5997 (3)	0.1931 (3)	0.56047 (11)	0.0614 (8)
C20	0.5545 (3)	0.3230 (3)	0.56423 (10)	0.0564 (7)
H20	0.506366	0.350888	0.595458	0.068*
C21	0.5812 (2)	0.4127 (3)	0.52098 (9)	0.0470 (5)
H21	0.550776	0.500543	0.523172	0.056*
C22	0.8280 (2)	0.6210 (2)	0.48858 (9)	0.0409 (5)
C23	0.8182 (3)	0.7555 (3)	0.50256 (11)	0.0554 (6)
H23	0.767663	0.812753	0.480217	0.067*
C24	0.8824 (3)	0.8051 (3)	0.54922 (11)	0.0654 (8)
H24	0.875209	0.895430	0.558020	0.078*
C25	0.9568 (3)	0.7223 (3)	0.58266 (11)	0.0638 (8)
H25	1.001936	0.756490	0.613547	0.077*
C26	0.9643 (3)	0.5877 (3)	0.57027 (11)	0.0592 (7)
H26	1.012596	0.530508	0.593452	0.071*
C27	0.9002 (2)	0.5375 (3)	0.52356 (10)	0.0489 (6)
H27	0.905754	0.446652	0.515529	0.059*
O3	0.5793 (3)	0.0972 (2)	0.60051 (10)	0.0965 (9)
C28	0.6814 (8)	0.170 (2)	0.2004 (3)	0.072 (3)	0.58 (3)
H28A	0.689965	0.129657	0.164219	0.108*	0.58 (3)
H28B	0.701082	0.264003	0.197712	0.108*	0.58 (3)
H28C	0.743336	0.128719	0.225846	0.108*	0.58 (3)
C28A	0.6531 (17)	0.097 (2)	0.2082 (6)	0.077 (4)	0.42 (3)
H28D	0.649827	0.068399	0.169996	0.115*	0.42 (3)
H28E	0.726058	0.159089	0.213058	0.115*	0.42 (3)
H28F	0.666519	0.021125	0.232053	0.115*	0.42 (3)
C29	0.5122 (5)	0.1347 (5)	0.65042 (14)	0.1075 (15)
H29A	0.504804	0.058414	0.674569	0.161*
H29B	0.562577	0.203758	0.668903	0.161*
H29C	0.423906	0.167462	0.641570	0.161*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0651 (12)	0.1163 (17)	0.0480 (11)	−0.0288 (13)	0.0180 (9)	−0.0358 (12)
O2	0.0643 (11)	0.0801 (12)	0.0422 (9)	−0.0337 (10)	0.0078 (8)	−0.0151 (9)
N1	0.0474 (10)	0.0396 (10)	0.0312 (9)	−0.0035 (8)	−0.0033 (8)	−0.0003 (8)
N2	0.0426 (10)	0.0429 (10)	0.0365 (9)	−0.0005 (9)	−0.0034 (8)	0.0012 (8)
C1	0.0550 (14)	0.0435 (13)	0.0398 (12)	−0.0069 (11)	0.0031 (10)	−0.0009 (10)
C2	0.0537 (15)	0.0620 (16)	0.0697 (18)	−0.0084 (13)	0.0029 (14)	−0.0045 (15)
C3	0.070 (2)	0.082 (2)	0.095 (3)	−0.0299 (18)	0.0199 (19)	−0.017 (2)
C4	0.111 (3)	0.080 (2)	0.085 (2)	−0.048 (2)	0.029 (2)	−0.002 (2)
C5	0.140 (4)	0.080 (2)	0.075 (2)	−0.029 (2)	−0.002 (2)	0.032 (2)
C6	0.088 (2)	0.0657 (18)	0.0657 (18)	−0.0185 (18)	−0.0106 (17)	0.0181 (15)
C7	0.0403 (11)	0.0387 (11)	0.0388 (11)	0.0004 (9)	−0.0030 (9)	−0.0009 (9)
C8	0.0413 (11)	0.0410 (12)	0.0340 (11)	0.0000 (10)	−0.0020 (9)	−0.0002 (9)
C9	0.0431 (11)	0.0348 (11)	0.0377 (11)	0.0009 (9)	−0.0031 (9)	−0.0001 (9)
C10	0.0402 (11)	0.0424 (12)	0.0330 (11)	−0.0017 (10)	−0.0045 (9)	0.0008 (9)
C11	0.0400 (11)	0.0558 (14)	0.0362 (11)	−0.0088 (11)	0.0038 (9)	−0.0002 (10)
C12	0.0506 (13)	0.0578 (14)	0.0297 (10)	−0.0060 (11)	0.0034 (10)	−0.0054 (10)
C13	0.0459 (12)	0.0493 (13)	0.0359 (11)	−0.0092 (11)	−0.0033 (10)	−0.0023 (10)
C14	0.0429 (12)	0.0574 (14)	0.0389 (12)	−0.0101 (11)	0.0075 (10)	−0.0011 (11)
C15	0.0494 (13)	0.0542 (13)	0.0293 (11)	−0.0030 (11)	0.0027 (10)	−0.0047 (10)
C16	0.0426 (11)	0.0412 (12)	0.0340 (11)	−0.0066 (9)	−0.0073 (9)	0.0038 (9)
C17	0.0552 (14)	0.0475 (13)	0.0486 (13)	−0.0032 (12)	−0.0087 (12)	−0.0012 (11)
C18	0.0795 (19)	0.0424 (13)	0.0636 (18)	−0.0080 (13)	−0.0222 (15)	0.0080 (12)
C19	0.0768 (18)	0.0589 (16)	0.0485 (15)	−0.0289 (15)	−0.0228 (14)	0.0163 (13)
C20	0.0570 (15)	0.0769 (19)	0.0353 (12)	−0.0179 (14)	−0.0040 (11)	0.0026 (12)
C21	0.0517 (13)	0.0507 (13)	0.0384 (12)	−0.0037 (11)	−0.0059 (11)	0.0001 (11)
C22	0.0442 (12)	0.0440 (12)	0.0346 (11)	−0.0060 (10)	−0.0015 (9)	−0.0017 (9)
C23	0.0743 (17)	0.0452 (12)	0.0469 (13)	−0.0039 (13)	−0.0074 (13)	−0.0018 (11)
C24	0.091 (2)	0.0526 (15)	0.0528 (16)	−0.0132 (15)	−0.0064 (15)	−0.0130 (13)
C25	0.0635 (17)	0.082 (2)	0.0455 (14)	−0.0230 (15)	−0.0082 (13)	−0.0146 (14)
C26	0.0534 (15)	0.0758 (19)	0.0485 (15)	−0.0010 (14)	−0.0139 (12)	0.0020 (13)
C27	0.0495 (13)	0.0493 (13)	0.0478 (13)	0.0008 (11)	−0.0070 (11)	−0.0040 (11)
O3	0.142 (2)	0.0828 (15)	0.0649 (14)	−0.0480 (16)	−0.0225 (15)	0.0333 (12)
C28	0.061 (4)	0.113 (8)	0.043 (3)	0.003 (5)	0.009 (3)	−0.017 (4)
C28A	0.074 (7)	0.081 (9)	0.075 (6)	0.004 (7)	0.005 (5)	−0.014 (6)
C29	0.130 (3)	0.134 (3)	0.058 (2)	−0.064 (3)	−0.010 (2)	0.041 (2)

Geometric parameters (Å, º) top

O1—C28A	1.232 (12)	C15—H15	0.9300
O1—C12	1.371 (3)	C16—C21	1.374 (3)
O1—C28	1.437 (10)	C16—C17	1.383 (3)
O2—C13	1.356 (3)	C17—C18	1.376 (4)
O2—H2A	0.8200	C17—H17	0.9300
N1—C8	1.367 (3)	C18—C19	1.371 (4)
N1—C9	1.395 (3)	C18—H18	0.9300
N1—C16	1.437 (3)	C19—O3	1.370 (3)
N2—C8	1.315 (3)	C19—C20	1.377 (4)
N2—C7	1.382 (3)	C20—C21	1.394 (3)
C1—C6	1.371 (4)	C20—H20	0.9300
C1—C2	1.390 (4)	C21—H21	0.9300
C1—C7	1.477 (3)	C22—C27	1.383 (3)
C2—C3	1.376 (4)	C22—C23	1.389 (4)
C2—H2	0.9300	C23—C24	1.379 (4)
C3—C4	1.348 (5)	C23—H23	0.9300
C3—H3	0.9300	C24—C25	1.368 (4)
C4—C5	1.364 (6)	C24—H24	0.9300
C4—H4	0.9300	C25—C26	1.380 (4)
C5—C6	1.401 (5)	C25—H25	0.9300
C5—H5	0.9300	C26—C27	1.380 (3)
C6—H6	0.9300	C26—H26	0.9300
C7—C9	1.363 (3)	C27—H27	0.9300
C8—C10	1.476 (3)	O3—C29	1.418 (5)
C9—C22	1.477 (3)	C28—H28A	0.9600
C10—C15	1.388 (3)	C28—H28B	0.9600
C10—C11	1.393 (3)	C28—H28C	0.9600
C11—C12	1.377 (3)	C28A—H28D	0.9600
C11—H11	0.9300	C28A—H28E	0.9600
C12—C13	1.391 (3)	C28A—H28F	0.9600
C13—C14	1.379 (3)	C29—H29A	0.9600
C14—C15	1.380 (3)	C29—H29B	0.9600
C14—H14	0.9300	C29—H29C	0.9600

C28A—O1—C12	124.3 (6)	C17—C16—N1	119.2 (2)
C12—O1—C28	116.5 (4)	C18—C17—C16	119.8 (3)
C13—O2—H2A	109.5	C18—C17—H17	120.1
C8—N1—C9	106.88 (18)	C16—C17—H17	120.1
C8—N1—C16	127.02 (18)	C19—C18—C17	120.4 (3)
C9—N1—C16	125.90 (17)	C19—C18—H18	119.8
C8—N2—C7	106.14 (17)	C17—C18—H18	119.8
C6—C1—C2	118.0 (3)	O3—C19—C18	115.3 (3)
C6—C1—C7	120.7 (2)	O3—C19—C20	124.4 (3)
C2—C1—C7	121.2 (2)	C18—C19—C20	120.3 (2)
C3—C2—C1	121.1 (3)	C19—C20—C21	119.7 (3)
C3—C2—H2	119.4	C19—C20—H20	120.2
C1—C2—H2	119.4	C21—C20—H20	120.2
C4—C3—C2	120.5 (3)	C16—C21—C20	119.6 (2)
C4—C3—H3	119.7	C16—C21—H21	120.2
C2—C3—H3	119.7	C20—C21—H21	120.2
C3—C4—C5	119.8 (3)	C27—C22—C23	118.3 (2)
C3—C4—H4	120.1	C27—C22—C9	122.5 (2)
C5—C4—H4	120.1	C23—C22—C9	119.1 (2)
C4—C5—C6	120.5 (3)	C24—C23—C22	120.7 (3)
C4—C5—H5	119.7	C24—C23—H23	119.7
C6—C5—H5	119.7	C22—C23—H23	119.7
C1—C6—C5	120.0 (3)	C25—C24—C23	120.5 (3)
C1—C6—H6	120.0	C25—C24—H24	119.8
C5—C6—H6	120.0	C23—C24—H24	119.8
C9—C7—N2	110.22 (19)	C24—C25—C26	119.5 (2)
C9—C7—C1	129.3 (2)	C24—C25—H25	120.2
N2—C7—C1	120.43 (19)	C26—C25—H25	120.2
N2—C8—N1	111.25 (19)	C25—C26—C27	120.2 (3)
N2—C8—C10	123.05 (19)	C25—C26—H26	119.9
N1—C8—C10	125.68 (19)	C27—C26—H26	119.9
C7—C9—N1	105.51 (18)	C26—C27—C22	120.7 (2)
C7—C9—C22	130.4 (2)	C26—C27—H27	119.6
N1—C9—C22	124.11 (19)	C22—C27—H27	119.6
C15—C10—C11	118.3 (2)	C19—O3—C29	118.3 (3)
C15—C10—C8	123.8 (2)	O1—C28—H28A	109.5
C11—C10—C8	117.76 (19)	O1—C28—H28B	109.5
C12—C11—C10	121.0 (2)	H28A—C28—H28B	109.5
C12—C11—H11	119.5	O1—C28—H28C	109.5
C10—C11—H11	119.5	H28A—C28—H28C	109.5
O1—C12—C11	124.0 (2)	H28B—C28—H28C	109.5
O1—C12—C13	115.7 (2)	O1—C28A—H28D	109.5
C11—C12—C13	120.4 (2)	O1—C28A—H28E	109.5
O2—C13—C14	118.8 (2)	H28D—C28A—H28E	109.5
O2—C13—C12	122.7 (2)	O1—C28A—H28F	109.5
C14—C13—C12	118.6 (2)	H28D—C28A—H28F	109.5
C13—C14—C15	121.3 (2)	H28E—C28A—H28F	109.5
C13—C14—H14	119.3	O3—C29—H29A	109.5
C15—C14—H14	119.3	O3—C29—H29B	109.5
C14—C15—C10	120.3 (2)	H29A—C29—H29B	109.5
C14—C15—H15	119.8	O3—C29—H29C	109.5
C10—C15—H15	119.8	H29A—C29—H29C	109.5
C21—C16—C17	120.3 (2)	H29B—C29—H29C	109.5
C21—C16—N1	120.5 (2)

C6—C1—C2—C3	−0.1 (4)	C10—C11—C12—C13	1.1 (4)
C7—C1—C2—C3	177.5 (3)	O1—C12—C13—O2	−1.0 (4)
C1—C2—C3—C4	−0.7 (5)	C11—C12—C13—O2	177.9 (2)
C2—C3—C4—C5	0.8 (6)	O1—C12—C13—C14	177.7 (2)
C3—C4—C5—C6	−0.1 (6)	C11—C12—C13—C14	−3.4 (4)
C2—C1—C6—C5	0.8 (4)	O2—C13—C14—C15	−178.3 (2)
C7—C1—C6—C5	−176.8 (3)	C12—C13—C14—C15	3.0 (4)
C4—C5—C6—C1	−0.8 (6)	C13—C14—C15—C10	−0.2 (4)
C8—N2—C7—C9	−0.7 (2)	C11—C10—C15—C14	−2.1 (3)
C8—N2—C7—C1	176.2 (2)	C8—C10—C15—C14	174.3 (2)
C6—C1—C7—C9	−141.3 (3)	C8—N1—C16—C21	−121.5 (3)
C2—C1—C7—C9	41.1 (4)	C9—N1—C16—C21	64.4 (3)
C6—C1—C7—N2	42.4 (3)	C8—N1—C16—C17	60.4 (3)
C2—C1—C7—N2	−135.2 (2)	C9—N1—C16—C17	−113.7 (3)
C7—N2—C8—N1	0.1 (2)	C21—C16—C17—C18	0.1 (4)
C7—N2—C8—C10	−178.6 (2)	N1—C16—C17—C18	178.2 (2)
C9—N1—C8—N2	0.6 (3)	C16—C17—C18—C19	−0.3 (4)
C16—N1—C8—N2	−174.4 (2)	C17—C18—C19—O3	−179.6 (2)
C9—N1—C8—C10	179.2 (2)	C17—C18—C19—C20	0.4 (4)
C16—N1—C8—C10	4.2 (4)	O3—C19—C20—C21	179.9 (2)
N2—C7—C9—N1	1.1 (2)	C18—C19—C20—C21	−0.1 (4)
C1—C7—C9—N1	−175.6 (2)	C17—C16—C21—C20	0.2 (3)
N2—C7—C9—C22	−180.0 (2)	N1—C16—C21—C20	−177.9 (2)
C1—C7—C9—C22	3.4 (4)	C19—C20—C21—C16	−0.1 (4)
C8—N1—C9—C7	−1.0 (2)	C7—C9—C22—C27	−126.7 (3)
C16—N1—C9—C7	174.1 (2)	N1—C9—C22—C27	52.1 (3)
C8—N1—C9—C22	180.0 (2)	C7—C9—C22—C23	49.6 (4)
C16—N1—C9—C22	−4.9 (3)	N1—C9—C22—C23	−131.6 (2)
N2—C8—C10—C15	−139.4 (2)	C27—C22—C23—C24	2.0 (4)
N1—C8—C10—C15	42.1 (3)	C9—C22—C23—C24	−174.4 (2)
N2—C8—C10—C11	37.0 (3)	C22—C23—C24—C25	−0.2 (5)
N1—C8—C10—C11	−141.5 (2)	C23—C24—C25—C26	−1.7 (5)
C15—C10—C11—C12	1.6 (3)	C24—C25—C26—C27	1.8 (4)
C8—C10—C11—C12	−175.0 (2)	C25—C26—C27—C22	0.1 (4)
C28A—O1—C12—C11	53.2 (16)	C23—C22—C27—C26	−1.9 (4)
C28—O1—C12—C11	14.6 (9)	C9—C22—C27—C26	174.4 (2)
C28A—O1—C12—C13	−127.9 (16)	C18—C19—O3—C29	177.1 (3)
C28—O1—C12—C13	−166.5 (9)	C20—C19—O3—C29	−2.9 (4)
C10—C11—C12—O1	180.0 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C9/N1/N2 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	2.28	2.718 (3)	114
O2—H2A···N2ⁱ	0.82	2.11	2.809 (3)	143
C4—H4···O2ⁱⁱ	0.93	2.55	3.379 (4)	148
C29—H29C···Cg1ⁱⁱⁱ	0.96	2.98	3.526 (5)	118

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1, y+1, z; (iii) −x−1, y+1/2, −z+3/2.

Funding information

Funding for this research was provided by: Science and Engineering Research Board (SERB), India EMEQ Scheme (grant No. EEQ2018/001373 to Nagarajan Loganathan); Rashtriya Uchchatar Shiksha Abhiyan, India Physical Sciences 2.0 (RUSA 2.0) (grant to Nagarajan Loganathan); Chief Minister Research Grant, Tamil Nadu, India (grant to Nagarajan Loganathan).

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